


Unforeseen Consequences of Messing with Witches

by Janice_Lester



Category: Supernatural
Genre: Drag Queens, Gen, Undercover
Language: English
Status: Completed
Published: 2011-08-06
Updated: 2011-08-06
Packaged: 2017-11-27 01:05:20
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,513
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/656319
Author URL: https://archiveofourown.org/users/Janice_Lester/pseuds/Janice_Lester
Summary: <blockquote class="userstuff">
              <p>Sam and Dean go undercover as drag queens.  This makes Castiel unusually curious.</p>
            </blockquote>





	Unforeseen Consequences of Messing with Witches

**Author's Note:**

> Written for the "cross-dressing" square of my [](http://kink-bingo.dreamwidth.org/profile)[kink_bingo](http://kink-bingo.dreamwidth.org/) card. Features the Winchesters in drag, among other things. Sam's efforts to explain drag culture should not be considered especially reliable information. Beta'd by [](http://ellethill.livejournal.com/profile)[ellethill](http://ellethill.livejournal.com/).

 

It’s kinda difficult, the Winchesters find, to go undercover in a club frequented by half a dozen witches who want to kill and/or punish them. It would be easier if the witches were, you know, evil and they could just take them out, but it turns out that these chicks (and one dude) are earth-communing, peace-loving, making-the-world-a-happier-place-one-daffodil-at-a-time kinda witches. They mean no harm to anyone. Even Cas says they lack evil intentions and take proper precautions against possible Dark influence. There’s just the tiny matter of Sam and Dean not having learned this stuff until they’d burst into the centre of their fairy ring, interrupted their chanting, and accused them of being responsible for the fifteen grisly supernatural murders that had taken place in town in the last four months. And dented honour is kind of a big deal for witches, apparently. Not only was their ritual ruined (they’d been summoning the spirit of spring, or something, to rehabilitate a polluted woodland area? Not Dean’s department, okay? Ask Sam), but they claimed they’d have to spend two weeks purifying their perfectly-understandable-Winchester-accusation-tarnished auras before they could resume their good works.

So, yeah, local coven? Not happy with the dashing Dean-and-Sam duo.

So they can’t just hang out in the club pretending to be ordinary patrons while they watch for what they now think is a particularly nasty species of tormented spirit picking its victims from this club. (This club where the witches hang out. You start to see why a handsome, caring man of action might have thought the said witches might have had something to do with the murders?) ‘Cause if the coven recognised them, that could be _embarrassing_.

Obviously, disguises were in order. And, obviously, Dean left that part up to Sam. Who is now perfectly turned out as the world’s tallest drag queen, and is _actually being chatted up for the position of club bouncer_. Kid actually seems to fit in here. Dean, meanwhile, is wearing…

Yeah.

Um, about that.

Not his idea, okay? Remember that. Not. His. Fucking. Idea.

Though, if anyone _can_ pull off a floor-length sleeveless white lace and velvet dress over a modestly-stuffed bra… _And_ he can actually walk in his heels, none of Sam’s clomping around like a baby giraffe and occasionally tripping over nothing at all. Dean definitely got the graceful genes, huh? Or maybe it’s an older brother thing? Bart Simpson totally whipped Lisa’s ass at walking in heels, too.

Speaking of ass, he’s finding it surprisingly pleasant to have dudes staring at his. Wanting what they can’t have. And it actually _isn’t_ unsexy to be wearing the kind of things he likes to see hot chicks wearing. Because the clothes _are_ sexy, all on their own. And the fabrics are lovely and soft and textured. And, while the procedure involved in hiding the boys from view (which Sam helpfully looked up on the internet for them) was… uh, _strange_ in a way he doesn’t like to think about too much, the final effect leaves him extra conscious of his junk and vaguely turned on all the time. It’s kinda cool. _Weird_ cool. Not his new favourite thing, but interesting.

“We should stay in town a while,” Sam says, when he escapes the club owner and comes to find Dean. “I think it’d be cool to work here. Though maybe not in this outfit. Not great for restraining difficult patrons in.”

“Dude,” Dean says, “it’s me. Don’t pretend like you don’t dig the outfit. And shouldn’t you be doing something with your voice? Making it all—” he clears his throat, changes pitch “—high and delicate and shit?”

Sam rolls his eyes. “You’ll only laugh. So, you seen any sign of ghosts?”

***

Dean’s balls are profoundly grateful to be released back into the wild, constrained only by the soft fabric of his underwear. And it’s nice to be able to swing his arms around normally without whacking himself in the fake boobies all the time. But still… that was kinda fun. And they have a lead on this week’s America’s Most Gankable.

“Hey, Sammy?” he calls. Sam pokes his head in the bathroom door. He’s half in, half out of his dress, bright green bra on display. “This shitty idea of yours didn’t turn out as bad as it could have.”

Sam snorts and departs in a frilly, lacy huff.

The plan is to stop by the Goodwill and leave their lady gear to find other homes. But, as he idly strokes the white velvet of his discarded dress, Dean kinda thinks he should hang on to this stuff. After all, it took serious time and effort to find outfits in his size. Not to mention the shoes. They just don’t seem to _make_ a whole heap of sexy high heels for Dean-Winchester-esque feet. And who knows when the whole outfit might come in useful again?

It’s right then, of course, that Cas shows up in a soft rustle of invisible wings.

“Oh,” he says, glancing from Sam half-dressed in a dress to Dean in his panties with a folded dress in his arms and a face full of ridiculous makeup, “has there been a change of fashion since I was last here?” He looks down at his own chest, grabs one side of his coat and fondles it unhappily. “Will I attract undue attention dressed like this?”

Dean opens his mouth to explain, then shuts it with a snap. Let it be Sam’s problem. He just wants to get this brightly-coloured crap off his face.

“We had to go out in disguise earlier tonight,” Sam starts to explain in his patient way.

“Disguised as women,” Cas says, as if he finally gets it.

“Um, no, not exactly…”

Dean smirks, even as he’s bent over the sink having a hard time getting his fancy mascara to come off.

“See, sometimes men—usually gay men, but not always—like to wear drag. Uh, to dress up as women, only not really, because everyone knows they’re not women. It’s more of a performance thing. Sometimes they lip-synch and dance to diva songs, and it’s all about being glamorous and eye-catching and sexy. Do you get it?”

Dean can almost hear him praying that Cas gets it.

“I’m not sure I fully understand,” Cas says slowly. “Dean?” he asks hopefully, turning his way.

Dean leaps to lock the bathroom door just in time.

And then Cas appears right behind him. _Angels_. “Dean?”

Wait for it. “Yeah, Cas?” Wait for it…

“You engaged in ‘drag’ this evening?”

“As rank amateurs, yeah.”

“So you understand the basic principles, at least?”

“Yeah. So?”

Cas frowns. “Could this phenomenon explain why my vessel chose to wear pink lace bikini briefs with this particular suit?”

That’s really a whole lot more than Dean ever needed to know. “No, I think that would probably be because wearing women’s panties turned him on.” _Guess he was a_ kinky _tax accountant…_

“How is that different?”

Dean begins to feel a headache coming on. “I don’t actually feel equipped to explain all the weird nooks and crannies of human sexuality right now, Cas. But how about we go on a field trip tomorrow and you can meet the nice drag queens? That might help. And we’ll, uh, buy you some nice manly boxers or something.”

“Really?” Cas asks, in a small voice. Which is really weird, but Dean can’t figure out what it means or what that new expression is he’s wearing, so he just shrugs and returns to scrubbing his face.

“Sure. No problem.”

***

It’s a day later, after they’ve field-tripped and researched and salted and burned, when he’s sprawling on the motel bed watching Cas fondle one of his brand new pairs of silky boxer shorts, that Dean begins to understand. It’s not just the fondling. There is also the fact that Cas has been attempting to conceal an erection—without, apparently, any real idea of just how that’s _done_ —since he ventured into the bathroom a half hour ago to swap Jimmy Novak’s pink lace panties for some more typical masculine fare.

Cas has been wearing women’s underwear for as long as he’s been down on Earth rocking the whole human-vessel look.

Cas has always worn women’s underwear.

He’s now wearing men’s underwear.

In a way, he’s cross-dressing.

And it’s turning him on.

“Uh, Cas?” Dean takes a deep breath. He probably shouldn’t say this. “Dude, if you know what jerking off is, now may be a good time to go someplace private and try that shit out, you know?”

Cas looks down at his lap, and frowns. Seems to be debating something. Meanwhile he’s formed the other pair of boxers into a ball and is gripping it tightly.

“You could keep them on,” Dean observes helpfully.

Cas looks like a lightbulb has gone on over his head. He offers Dean a grateful half-smile. And then he’s gone.

It’s weird, Dean thinks, as he’s settling down for a well-deserved nap, how sometimes the weirdest things in his life aren’t actually the monsters.

 

***END***


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